Epichlorohydrin → HCID 76010298、化合物

HRID 1157977ノート

反応式

HRID 1157977 の反応式
[OH:1][C:2]1[CH:19]=[CH:18][C:5]([C:6](=[O:17])[CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:22]([CH:24]1[O:26][CH2:25]1)Cl>CN(C)C=O>[O:26]1[CH2:25][CH:24]1[CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:17])[CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:18][CH:19]=1

参加物

5

反応物 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 97793HCID 97793、化合物2 回

生成物 1

HCID 76010298HCID 76010298、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a well-stirred solution of 4′-hydroxy-4-methoxy-chalcone, 7 (15 g, 59 mmol) in dry dimethyl formamide (170 mL) was added 50% sodium hydride (5.6 g, 236 mmol) at 0-5° C. and after 30 minutes, excess of epichlorohydrin (13.8 mL, 177 mmol) was added and stirred at room temperature for overnight. The reaction mixture was concentrated under reduced pressure, diluted with water and extracted with chloroform. The combined organic layers were dried over sodium sulphate, filtered and evaporated to dryness. The crude product was purified by column chromatography to afford 13. Yield 11 g (60%); mp 85-87° C.; MS (FAB) 311 (M++1); IR (KBr) 1655; 1H NMR (200 MHz, CDCl3) δ 8.02 (d, J=8.8 Hz, 2H), 7.77 (d, J=15.6 Hz, 1H), 7.59 (d, J=8.7 Hz, 2H), 7.41 (d, J=15.6 Hz, 1H), 6.99 (d, J=8.8 Hz, 2H), 6.93 (d, J=8.7 Hz, 2H), 4.32 (dd, J=11.1 Hz, 2.9 Hz, 1H), 4.01 (dd, J=11.1 Hz, 5.7 Hz, 1H), 3.84 (s, 31H), 3.40-3.35 (m, 1H), 2.92 (t, J=4.5 Hz, 4.5 Hz, 1H), 2.77 (dd, J=4.8 Hz, 2.6 Hz, 1H).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionextracted with chloroform
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-1aed249538c84b8b95abdd0a95581614
出典データセット
uspto-grants-2010_10
特許番号
US07807712B2

反応ノート

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